I would say that you're missing the fact that weaknessless, eventfulnessless, timelinessless are not real words.
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Peter Shor Nov 19 '12 at 1:17

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This is a debated point. There are linguistics papers on this topic, e.g., Parsing is not weaknessless: suffix ordering revisited // And the two other examples you give are specious. The first is in someone's blog, and the second is from an illiterate comment about a neurologist.
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user21497Nov 19 '12 at 1:20

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@BillFranke I found a 1970 paper that investigates why productive -less is blocked on nominalizations ending not only in -ness, but also those ending in -ity and -ment. You can't have something that is *continuitiless, *probabilitiless, *investmentless, or *measurementless, either.
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tchristNov 19 '12 at 4:10

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I'm not sure that "Eventfulnessless" in your first example is used as a noun; in English we can use many parts of speech as titles.
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Mark BeadlesNov 19 '12 at 16:25

Another example is witnessless. Here witness indeed etymologically has the suffix -ness, although the meaning has now drifted away from the original, so that this isn't apparent to English speakers.
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Peter Shor Nov 19 '12 at 10:50

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@bytebuster Well, there’s something about it here, but I can’t read more of the paper.
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tchristNov 19 '12 at 12:52

@PeterShor -- how far can this be recursed? Can a case be dismissed on the grounds of witnesslessnesss? If a lawyer never suffers such a dismissal, is he witnesslessnesssless?
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MalvolioMay 11 at 19:48

As you can see, this makes for rather a reciprocal definition: -ness takes adjectives and makes them nouns; -less takes nouns and makes them adjectives.

In other words:

If you take a base noun (say, spot) and add -less, you create a new word: a derived adjective, spotless. Add -ness to that, and you create another new word: a derived noun, spotlessness.

If you take a base adjective (say, kind) and add -ness, you create a derived noun, kindness. Add -less to that, and you create a derived adjective, kindnessless.

Recursion

In both these cases, you could theoretically continue the cycle ad nauseam, or at least until you no longer have the faintest idea what what you’re saying is supposed to mean (is something that is spotlessnesslessnesslessnessless clean or dirty? Heaven knows!). This process is part of what is known as recursion: applying a process to an input that is itself the result of the process you’re applying.

Continuing the cycle more than once or twice is highly impractical, obviously, but it does plays perfectly by the rules of English morphology, and the main reason it’s not practically usable is that English speakers cannot keep that level of abstraction and repeated negation in their heads. That’s a semantic constraint, a limitation in the part of our brains that attach logical meaning to the words we hear, once they’ve been parsed.

The only morphological limitation to using these suffixes productively is that -ness must be added to adjectives and -less to nouns. As such, there is no possible order between the two: they cannot appear in the same place, which rules out any internal ordering of them, as ‘ordering’ implies structurally parallel elements. In spotlessness, it is not the case that both -less and -ness equally and simultaneously modify spot; rather, -less modifies spot, while -ness modifies not spot, but spotless.

Testing

The simplest way to verify that this is so is simply to take some of the words combining both suffixes and reverse the suffixes. You will find very quickly that this is not possible in either direction. If there were any kind of internal ordering rule going on here, you would expect that one order always won out, which is not the case:

1 I’m ignoring here the humorous broadening of -ness to be used with just about any noun. Things like houseness or foreheadness do exist and are used, but they’re a different kettle of fish not directly related to this question.

2 The root word here is of course time, which is a noun; but the derivational base to which -ness is added is timely, which is a derived adjective just like timeless would be. (-ly is most commonly used to derive adverbs from adjectives, but it can also be used to derive adjectives from a variety of sources: timely, comely, gainly, etc.)

The -ness suffix makes an abstract noun out of a word. The -less suffix means being without something. So [root]-less-ness is the abstract condition of being without the root. [root]-ness-less is being without the abstract condition based on the root.

It took me a while to parse this, and I'm guessing whoever downvoted just found this answer too difficult to understand (or difficult enough not to be useful). I will say that I get and agree with the gist of this (ultimately, it says what I would have said if I bothered to answer this question), but I think it would be more effective and accessible if it used real examples (such as weaknessless in the OP's question).
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John YApr 29 '14 at 4:28

Well, my answer does contradict the accepted answer that the -nessless ending is "impossible," but personally I found neither that contention nor the cited source to be convincing, especially given the counterexamples people found.
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Chris SunamiApr 29 '14 at 12:59